NP-MRD: Showing NP-Card for vanchrobactin (NP0035319)

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Record Information

Version

2.0

Created at

2021-06-20 18:47:50 UTC

Updated at

2021-06-30 00:06:13 UTC

NP-MRD ID

NP0035319

Secondary Accession Numbers

None

Natural Product Identification

Common Name

vanchrobactin

Provided By

JEOL Database JEOL Logo

Description

Vanchrobactin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. vanchrobactin is found in Vibrio anguillarum and Vibrio sp. DS40M4. vanchrobactin was first documented in 2006 (PMID: 17159203). Based on a literature review a small amount of articles have been published on vanchrobactin (PMID: 18005167) (PMID: 18362969) (PMID: 18451049) (PMID: 19270115).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120473D          

 51 51  0  0  0  0            999 V2000
    0.3218   -3.7349    1.9194 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -2.7158    1.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.7960    0.4292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835   -1.4442    1.8179 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -1.0347    2.8131 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0831    0.4812    2.7809 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9178    0.9810    1.5912 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2194    0.9557    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0464    1.8337    0.2062 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    1.3997    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.2094    0.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    2.4504   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    2.0278   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957    2.9530   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4218    4.3161   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982    4.7371   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661    6.0616   -0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0463    3.8197   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    4.3217   -0.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978    1.4058   -0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    1.1591   -0.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6196    2.0488   -1.9498 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    2.2705   -3.2570 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2030    2.7954   -4.2467 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0138    2.0019   -4.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    3.2362   -3.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182    3.9517   -4.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    3.1716   -2.2295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069   -4.5720    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -1.9427    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -3.6718    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087   -0.7403    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1219    1.0064    2.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256    0.7553    3.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    0.3996    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    2.0144    1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -0.0597   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0  0  0  0
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  7 38  1  0  0  0  0
  8 39  1  6  0  0  0
 22 46  1  0  0  0  0
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  1 29  1  0  0  0  0
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 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
 28 51  1  0  0  0  0
 25 50  1  0  0  0  0
M  END

     RDKit          3D

 51 51  0  0  0  0  0  0  0  0999 V2000
    0.3218   -3.7349    1.9194 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -2.7158    1.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6196    2.0488   -1.9498 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202120473D          

 51 51  0  0  0  0            999 V2000
    0.3218   -3.7349    1.9194 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -2.7158    1.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5770    2.7563   -5.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734    2.3019   -4.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863    2.4125   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 10 12  1  0  0  0  0
  8 20  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  2  0  0  0  0
 20 22  1  0  0  0  0
 13 14  1  0  0  0  0
  5  6  1  0  0  0  0
 14 15  2  0  0  0  0
 22 23  1  0  0  0  0
 15 16  1  0  0  0  0
  2  4  1  0  0  0  0
 16 18  2  0  0  0  0
 18 12  1  0  0  0  0
 23 26  1  0  0  0  0
 16 17  1  0  0  0  0
  6  7  1  0  0  0  0
 18 19  1  0  0  0  0
  2  1  2  3  0  0  0
 20 21  2  0  0  0  0
  3  2  1  0  0  0  0
 23 24  1  0  0  0  0
  8  9  1  0  0  0  0
 26 28  1  0  0  0  0
  8  7  1  0  0  0  0
 24 25  1  0  0  0  0
  9 10  1  0  0  0  0
 26 27  2  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
  8 39  1  6  0  0  0
 22 46  1  0  0  0  0
 23 47  1  6  0  0  0
  1 29  1  0  0  0  0
  9 40  1  0  0  0  0
 13 41  1  0  0  0  0
 14 42  1  0  0  0  0
 15 43  1  0  0  0  0
 17 44  1  0  0  0  0
 19 45  1  0  0  0  0
 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
 28 51  1  0  0  0  0
 25 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035319

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])C(=O)[C@]([H])(N([H])C(=O)C1=C([H])C([H])=C([H])C(O[H])=C1O[H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H23N5O7/c17-16(18)19-6-2-4-9(14(26)21-10(7-22)15(27)28)20-13(25)8-3-1-5-11(23)12(8)24/h1,3,5,9-10,22-24H,2,4,6-7H2,(H,20,25)(H,21,26)(H,27,28)(H4,17,18,19)/t9-,10+/m1/s1

> <INCHI_KEY>
LXNCWECCTQQXPQ-ZJUUUORDSA-N

> <FORMULA>
C16H23N5O7

> <MOLECULAR_WEIGHT>
397.388

> <EXACT_MASS>
397.159748101

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.90774421213311

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2R)-5-carbamimidamido-2-[(2,3-dihydroxyphenyl)formamido]pentanamido]-3-hydroxypropanoic acid

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
-3.0038696561947766

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.281774974900195

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8372461083872427

> <JCHEM_PKA_STRONGEST_BASIC>
12.101407079347343

> <JCHEM_POLAR_SURFACE_AREA>
218.08999999999997

> <JCHEM_REFRACTIVITY>
106.84029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2R)-5-carbamimidamido-2-[(2,3-dihydroxyphenyl)formamido]pentanamido]-3-hydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 51  0  0  0  0  0  0  0  0999 V2000
    0.3218   -3.7349    1.9194 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -2.7158    1.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.7960    0.4292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835   -1.4442    1.8179 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -1.0347    2.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831    0.4812    2.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178    0.9810    1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2194    0.9557    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0464    1.8337    0.2062 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    1.3997    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.2094    0.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    2.4504   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    2.0278   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957    2.9530   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4218    4.3161   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982    4.7371   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661    6.0616   -0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0463    3.8197   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    4.3217   -0.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978    1.4058   -0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    1.1591   -0.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6196    2.0488   -1.9498 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    2.2705   -3.2570 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2030    2.7954   -4.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138    2.0019   -4.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    3.2362   -3.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182    3.9517   -4.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    3.1716   -2.2295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069   -4.5720    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -1.9427    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -3.6718    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087   -0.7403    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8326   -1.5423    2.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984   -1.3220    3.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219    1.0064    2.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256    0.7553    3.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    0.3996    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    2.0144    1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -0.0597   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042    2.8413    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8869    0.9682    0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7259    2.6031   -0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2442    5.0218   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886    6.5823   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    5.2939   -0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016    2.0695   -1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181    1.2899   -3.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9260    3.8298   -4.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770    2.7563   -5.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734    2.3019   -4.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863    2.4125   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 10 12  1  0
  8 20  1  0
 10 11  2  0
 12 13  2  0
 20 22  1  0
 13 14  1  0
  5  6  1  0
 14 15  2  0
 22 23  1  0
 15 16  1  0
  2  4  1  0
 16 18  2  0
 18 12  1  0
 23 26  1  0
 16 17  1  0
  6  7  1  0
 18 19  1  0
  2  1  2  3
 20 21  2  0
  3  2  1  0
 23 24  1  0
  8  9  1  0
 26 28  1  0
  8  7  1  0
 24 25  1  0
  9 10  1  0
 26 27  2  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  6
 22 46  1  0
 23 47  1  6
  1 29  1  0
  9 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 19 45  1  0
 24 48  1  0
 24 49  1  0
 28 51  1  0
 25 50  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  N   UNK     0       0.322  -3.735   1.919  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.278  -2.716   1.424  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.173  -2.796   0.429  0.00  0.00           N+0
HETATM    4  N   UNK     0      -0.084  -1.444   1.818  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.873  -1.035   2.813  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.083   0.481   2.781  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.918   0.981   1.591  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.219   0.956   0.225  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.046   1.834   0.206  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.249   1.400   0.079  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.551   0.209   0.056  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.308   2.450  -0.016  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.648   2.028  -0.003  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.696   2.953  -0.089  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.422   4.316  -0.194  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.098   4.737  -0.211  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.766   6.062  -0.314  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.046   3.820  -0.124  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.767   4.322  -0.154  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.198   1.406  -0.887  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.403   1.159  -0.895  0.00  0.00           O+0
HETATM   22  N   UNK     0       1.620   2.049  -1.950  0.00  0.00           N+0
HETATM   23  C   UNK     0       2.258   2.271  -3.257  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.203   2.795  -4.247  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.014   2.002  -4.163  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.456   3.236  -3.290  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.718   3.952  -4.251  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.290   3.172  -2.229  0.00  0.00           O+0
HETATM   29  H   UNK     0      -0.007  -4.572   1.439  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.537  -1.943   0.016  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.425  -3.672   0.002  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.709  -0.740   1.435  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.833  -1.542   2.663  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.498  -1.322   3.802  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.122   1.006   2.825  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.626   0.755   3.695  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.847   0.400   1.544  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.222   2.014   1.807  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.922  -0.060  -0.050  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.204   2.841   0.224  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.887   0.968   0.079  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.726   2.603  -0.074  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.244   5.022  -0.260  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.589   6.582  -0.351  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.889   5.294  -0.230  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.602   2.070  -1.957  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.618   1.290  -3.591  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.926   3.830  -4.014  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.577   2.756  -5.276  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.573   2.302  -4.881  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.086   2.413  -1.630  0.00  0.00           H+0
CONECT    1    2   29                                                       
CONECT    2    4    1    3                                                  
CONECT    3    2   30   31                                                  
CONECT    4    5    2   32                                                  
CONECT    5    4    6   33   34                                             
CONECT    6    5    7   35   36                                             
CONECT    7    6    8   37   38                                             
CONECT    8   20    9    7   39                                             
CONECT    9    8   10   40                                                  
CONECT   10   12   11    9                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   41                                                  
CONECT   14   13   15   42                                                  
CONECT   15   14   16   43                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16   44                                                       
CONECT   18   16   12   19                                                  
CONECT   19   18   45                                                       
CONECT   20    8   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   23   46                                                  
CONECT   23   22   26   24   47                                             
CONECT   24   23   25   48   49                                             
CONECT   25   24   50                                                       
CONECT   26   23   28   27                                                  
CONECT   27   26                                                            
CONECT   28   26   51                                                       
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   24                                                            
CONECT   50   25                                                            
CONECT   51   28                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  102    0
END

RDKit          3D

51 51  0  0  0  0  0  0  0  0999 V2000
    0.3218   -3.7349    1.9194 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -2.7158    1.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731   -2.7960    0.4292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835   -1.4442    1.8179 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8726   -1.0347    2.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831    0.4812    2.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178    0.9810    1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2194    0.9557    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0464    1.8337    0.2062 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    1.3997    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.2094    0.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081    2.4504   -0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    2.0278   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6957    2.9530   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4218    4.3161   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982    4.7371   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661    6.0616   -0.3141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0463    3.8197   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    4.3217   -0.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978    1.4058   -0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    1.1591   -0.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6196    2.0488   -1.9498 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    2.2705   -3.2570 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2030    2.7954   -4.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138    2.0019   -4.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    3.2362   -3.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7182    3.9517   -4.2509 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    3.1716   -2.2295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069   -4.5720    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -1.9427    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -3.6718    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087   -0.7403    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8326   -1.5423    2.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984   -1.3220    3.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219    1.0064    2.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256    0.7553    3.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    0.3996    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    2.0144    1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -0.0597   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042    2.8413    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8869    0.9682    0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7259    2.6031   -0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2442    5.0218   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886    6.5823   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    5.2939   -0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016    2.0695   -1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181    1.2899   -3.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9260    3.8298   -4.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770    2.7563   -5.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734    2.3019   -4.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863    2.4125   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 10 12  1  0
  8 20  1  0
 10 11  2  0
 12 13  2  0
 20 22  1  0
 13 14  1  0
  5  6  1  0
 14 15  2  0
 22 23  1  0
 15 16  1  0
  2  4  1  0
 16 18  2  0
 18 12  1  0
 23 26  1  0
 16 17  1  0
  6  7  1  0
 18 19  1  0
  2  1  2  3
 20 21  2  0
  3  2  1  0
 23 24  1  0
  8  9  1  0
 26 28  1  0
  8  7  1  0
 24 25  1  0
  9 10  1  0
 26 27  2  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  6
 22 46  1  0
 23 47  1  6
  1 29  1  0
  9 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 19 45  1  0
 24 48  1  0
 24 49  1  0
 28 51  1  0
 25 50  1  0
M  END

View in JSmol

Synonyms

Value	Source
N-[N'-(2,3-dihydroxybenzoyl)-D-arginyl]-L-serine	ChEBI
N(2)-(2,3-Dihydroxybenzoyl)-D-arg-L-ser	ChEBI

Chemical Formula

C₁₆H₂₃N₅O₇

Average Mass

397.3880 Da

Monoisotopic Mass

397.15975 Da

IUPAC Name

(2S)-2-[(2R)-5-carbamimidamido-2-[(2,3-dihydroxyphenyl)formamido]pentanamido]-3-hydroxypropanoic acid

Traditional Name

(2S)-2-[(2R)-5-carbamimidamido-2-[(2,3-dihydroxyphenyl)formamido]pentanamido]-3-hydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]([H])(N([H])C(=O)[C@]([H])(N([H])C(=O)C1=C([H])C([H])=C([H])C(O[H])=C1O[H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C16H23N5O7/c17-16(18)19-6-2-4-9(14(26)21-10(7-22)15(27)28)20-13(25)8-3-1-5-11(23)12(8)24/h1,3,5,9-10,22-24H,2,4,6-7H2,(H,20,25)(H,21,26)(H,27,28)(H4,17,18,19)/t9-,10+/m1/s1

InChI Key

LXNCWECCTQQXPQ-ZJUUUORDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vibrio anguillarum	LOTUS Database	35616633
Vibrio campbellii DS40M4	JEOL database	Sandy, M., et al, J. Nat. Prod. 73, 1038 (2010)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.81	ALOGPS
logP	-3	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	12.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	218.09 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	106.84 m³·mol⁻¹	ChemAxon
Polarizability	38.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17591618

KEGG Compound ID

Not Available

BioCyc ID

CPD-21007

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

157682

Good Scents ID

Not Available

References

General References

Balado M, Osorio CR, Lemos ML: A gene cluster involved in the biosynthesis of vanchrobactin, a chromosome-encoded siderophore produced by Vibrio anguillarum. Microbiology (Reading). 2006 Dec;152(Pt 12):3517-3528. doi: 10.1099/mic.0.29298-0. [PubMed:17159203 ]
Naka H, Lopez CS, Crosa JH: Reactivation of the vanchrobactin siderophore system of Vibrio anguillarum by removal of a chromosomal insertion sequence originated in plasmid pJM1 encoding the anguibactin siderophore system. Environ Microbiol. 2008 Jan;10(1):265-77. doi: 10.1111/j.1462-2920.2007.01450.x. Epub 2007 Nov 13. [PubMed:18005167 ]
Soengas RG, Larrosa M, Balado M, Rodriguez J, Lemos ML, Jimenez C: Synthesis and biological activity of analogues of vanchrobactin, a siderophore from Vibrio anguillarum serotype O2. Org Biomol Chem. 2008 Apr 7;6(7):1278-87. doi: 10.1039/b719713f. Epub 2008 Feb 29. [PubMed:18362969 ]
Balado M, Osorio CR, Lemos ML: Biosynthetic and regulatory elements involved in the production of the siderophore vanchrobactin in Vibrio anguillarum. Microbiology (Reading). 2008 May;154(Pt 5):1400-1413. doi: 10.1099/mic.0.2008/016618-0. [PubMed:18451049 ]
Balado M, Osorio CR, Lemos ML: FvtA is the receptor for the siderophore vanchrobactin in Vibrio anguillarum: utility as a route of entry for vanchrobactin analogues. Appl Environ Microbiol. 2009 May;75(9):2775-83. doi: 10.1128/AEM.02897-08. Epub 2009 Mar 6. [PubMed:19270115 ]
Sandy, M., et al. (2010). Sandy, M., et al, J. Nat. Prod. 73, 1038 (2010). J. Nat. Prod..

Showing NP-Card for vanchrobactin (NP0035319)

MOL for NP0035319 (vanchrobactin)

3D MOL for NP0035319 (vanchrobactin)

3D SDF for NP0035319 (vanchrobactin)

3D-SDF for NP0035319 (vanchrobactin)

PDB for NP0035319 (vanchrobactin)

3D PDB for NP0035319 (vanchrobactin)

SMILES for NP0035319 (vanchrobactin)

INCHI for NP0035319 (vanchrobactin)

Structure for NP0035319 (vanchrobactin)

3D Structure for NP0035319 (vanchrobactin)